Hydrochloric Acid → HCID 23111791, compound

HRID 1163317Notes

Reaction equation

HRID 1163317 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][CH:33]=1)[CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]2[CH:21]([CH2:24][C:25]([O:27]C)=[O:26])[CH2:22][O:23][C:19]=2[CH:18]=1.CO.[OH-].[Na+].Cl>O.O1CCCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][CH:33]=1)[CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]2[CH:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][O:23][C:19]=2[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58755241HCID 58755241, compound

Product 1

HCID 23111791HCID 23111791, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (6-{[3-(2-methyl-1-naphthyl)benzyl]oxy}-2,3-dihydro-1-benzofuran-3-yl)acetate (0.801 g, 1.90 mmol) in a mixed solvent of methanol (6 mL) and tetrahydrofuran (6 mL) was added 2 M aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at room temperature for 20 hr. Water was added to the reaction mixture, and the mixture was acidified with 1 M hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane-ethyl acetate), and recrystallized from ethyl acetate-hexane to give the title compound (0.444 g, yield 55%) as colorless needle crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane-ethyl acetate)
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d4e2337e89744542953fcf32833c6537
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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